Neighborhood · Winter Park, Florida
Windsong Lakeside
Lakeside living inside one of Winter Park's finest addresses
Windsong Lakeside sits among the lakes that give this pocket of Winter Park its reputation, a short reach from the boutiques and dining around Hannibal Square and the shoreline of Lake Killarney. It's a quiet, established community where families settle in for the long haul, drawn to the tree-lined streets and the walkable proximity to central Winter Park. Homes here trade rarely, and when they do, they tend to be substantial residences rather than starter houses.
For a buyer today, the reality is scarcity. There are no active listings on the market right now, and only three homes sold in Windsong Lakeside over the past year — at a median sold price of $2,700,000. If you want in, patience and a ready pre-approval matter more than browsing; the same holds for nearby enclaves like Winter Park Pines and Eastbrook.
Windsong Lakeside is a community in Winter Park, Florida.
Quick facts
3 sold in 12 months
On the market now
Homes for sale in Windsong Lakeside
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
Every active listing inside the Windsong Lakeside boundary
Open full map search →The numbers that matter
The Windsong Lakeside market
3
Sold, last 12 months
$2,700,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
2 days
Median time to sell
Windsong Lakeside vs Winter Park
Median sold price — 3-yr, 3-mo rolling
▲ 16.2% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windsong Lakeside boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsong Lakeside is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
282
Median age
47
Median income
$223,002
Median home value
$832,519
Beyond the listings
Living in Windsong Lakeside
Culture
Top 4% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Beliefs
Top 10% in the U.S.Politically Engaged
Politically aware, this population is interested in civic issues on both the local and national level. They often discuss candidates for office, taxes, and political ideologies.
Appearance oriented
Top 11% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Lifestyles
Top 11% in the U.S.Daily Grind
Whether throwing punches at the boxing club or punching the clock at work, this population likes to talk about their hard work.
Relationships
Top 13% in the U.S.Family Time
Family time is always a good time for these folks. Whether it's a family vacation or making ice cream sundaes at home, this population loves spending time with the people closest to them.
Relationships
Top 14% in the U.S.Dating Life
With dating comes highs, lows, and lots of questions. You can find this population talking about dating advice, breakups and how to express their feelings.
People who close here
Our Winter Park experts
Straight answers
Windsong Lakeside FAQs
Is Windsong Lakeside a good place to live?+
It's one of Winter Park's more desirable lakeside communities, prized for its quiet streets and proximity to the shops and restaurants around Hannibal Square. Families are drawn to the strong school assignment — Winter Park High, Glenridge Middle, and Brookshire Elementary — and to the walkable central Winter Park lifestyle.
Is Windsong Lakeside expensive?+
Yes — this is a luxury market. The three homes that sold over the past year did so at a median price of $2,700,000, placing it well above typical Winter Park pricing and firmly in high-end territory.
What do homes cost in Windsong Lakeside?+
Recent sales point to the multi-million-dollar range, with a median sold price of $2,700,000 over the last 12 months. There are no active listings at the moment, so pricing on the next available home will depend heavily on its size and lake access.
How is the market in Windsong Lakeside?+
It's a very low-inventory, high-demand market — only three homes changed hands in the past year and there are currently zero active listings. Sellers averaged 97% of their asking price, so serious buyers should be ready to move quickly when something comes up, or consider nearby options like Winter Park Pines.
What about HOA fees and property taxes?+
Specific HOA and tax figures aren't available for the small number of recent sales here. As with any high-value Winter Park property, we can pull the exact assessments and any community dues for a specific address once one comes to market.
Keep exploring
More Winter Park neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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